Triethylamine → N-[(2-bromophenyl)methyl]cyclopropanamine

To a THF solution (0.15 M) of 2-bromobenzyl alcohol (1 eq.) was added triethylamine (1.6 eq.). The reaction mixture was cooled to 0° C. before methanesulfonyl chloride (1.3 eq.) was added dropwise. The resulting solution was then allowed to warm slowly to RT. After 1.5 h, cyclopropylamine (5 eq.) was added to the now cloudy suspension. After another 18 h, the reaction mixture was diluted with ether and quenched with 1 N aq. NaOH. The organic extract was separated, washed with brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 4:1 (v/v) Hex:EtOAc→1:4 (v/v) Hex:EtOAc) afforded the title compound as a light yellow oil.

1. additionwas added dropwise
2. waitAfter another 18 h
3. customquenched with 1 N aq. NaOH
4. extractionThe organic extract
5. customwas separated
6. washwashed with brine
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationthe filtrate concentrated in vacuo
10. customPurification of the crude product
11. customthus obtained by way of flash chromatography (SiO2, 4:1 (v/v) Hex:EtOAc→1:4 (v/v) Hex:EtOAc)

ORD-Eintrag

ord-f633d0e0cfd84eb683073d3090833983

Quelldatensatz

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08889714B2